Nitrogen-containing organosilicon compound method of manufacture, and method of treating surfaces

ABSTRACT

A new nitrogen-containing organosilicon compound contains tertiary amine groups and carbonyl groups wherein the tertiary amine groups are selected from R 1 R 2 N— (where R 1  and R 2  are the same or different univalent hydrocarbon groups of 1-15 carbon atoms), alicyclic amino groups, or heterocyclic amino groups containing in their rings one or more tertiary amine groups.

CROSS-RFERENCE TO RELATED APPLICATIONS

This present application is a divisional of Ser. No. 10/551,528, whichwas filed On Aug. 24, 2006, now U.S. Pat. No. 7,326,800 which claimspriority to and all the advantages of International Application No.PCT/JP2004/004562, filed on Mar. 30, 2004, which claims priority toJapanese Patent Application No. JP 2003-093337, filed Mar. 31, 2003.

FIELD OF THE INVENTION

This invention is related to a nitrogen-containing organosiliconcompound and to a method of manufacture, as well as to a silane couplingagent prepared from the nitrogen-containing organosilicon compound.

BACKGROUND OF THE INVENTION

Organosilicon compounds that contain amino groups and alkoxysilyl groupsare used as silane coupling agents. For example, alkoxysilanes thatcontain primary amino groups and expressed by the formulaeH₂NC₃H₆Si(OC₂H₅)₃ and H₂NC₂H₄NHC₃H₆Si(OCH₃)₃ are known. However, adisadvantage of such compounds is that when compounds that containprimary amino groups are used in conjunction with organic resins, suchas epoxy resins that utilize amines as curing catalysts, the amino-groupcontaining compounds exert an adverse effect on the curability of theresins. Therefore, it has been proposed to use alkoxysilanes of theformulae shown as disclosed in U.S. Pat. No. 5,476,884 and JP2002-193976 A, with secondary amino groups such as PhNHC₃H₆Si(OCH₃)₃where Ph is a phenyl group,

-   CH₃(CH₂)₃NHC₃H₆Si(OCH₃)₃, or alkoxysilanes with tertiary amino    groups such as (C₄H₉)₂NC₃H₆Si(OCH₃)₃.

Although the alkoxysilanes with such secondary or tertiary amino groupsreduce the effect on curability of the resins to some extent, theiradhesion-improving effect with respect to various substrates isinsignificant, and their silane coupling function is insufficient.Another disadvantage of the last mentioned compounds is that, in themanufacturing process, they produce a large amount of by-products in theform of amine hydrochloric salts.

On the other hand, organosilicon compounds with amide groups are knownin the art including alkoxysilanes such as

-   H₂NCONHC₃H₆Si(OC₂H₅)₃ and H₂NCOC₃H₆Si(OC₂H₅)₃ as in U.S. Pat. No.    3,033,815 (May 8, 1962). Furthermore, U.S. Pat. No. 4,209,455 (Jun.    24, 1980) discloses alkoxysilanes which contain secondary amide    groups such as H₂NC₂H₄NHCOC₃H₆Si(OC₂H₅)₃ and-   C₁₈H₃₇NHCOC₂H₄NHC₃H₆Si(OC₂H₅)₃.

However, even these alkoxysilanes still exert unfavorable effect oncurability and adhesion-imparting properties of the resins, andtherefore are not yet sufficient in their function as silane couplingagents.

SUMMARY OF THE INVENTION

It is therefore an object of the present invention to provide novelnitrogen-containing organosilicon compounds with tertiary amino andcarbonyl groups.

It is another object to provide a method for manufacturing suchnitrogen-containing compounds, and silane coupling agents prepared fromthese nitrogen-containing organosilicon compounds.

These and other features of the invention will become apparent from aconsideration of the detailed description.

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 is a graph that shows an IR spectrum of the nitrogen-containingorganosilicon compound obtained in Practical Example 1.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to nitrogen-containing organosiliconcompounds of the following general Formula (I) and to a method formanufacturing the compounds

where R¹ and R² are the same or different univalent hydrocarbon groupswith 1-15 carbon atoms, R³ is a bivalent hydrocarbon group with 1-15carbon atoms, or an alkyleneoxy group of the formula —C_(n)H_(2n)O—where n is an integer from 1-15; R⁴ is a bivalent hydrocarbon group with1-15 carbon atoms; R⁵ is a univalent hydrocarbon group with 1-15 carbonatoms; R⁶ is a univalent hydrocarbon group with 1-15 carbon atoms or analkoxyalkyl group; R⁷ is an alkyl group such as methyl or a hydrogenatom; R⁸ is a hydrogen atom, an alkyl group with 1-20 carbon atoms, oran aryl group; m is 0 or 1; x is 0-2; and y is 1-5.

The invention also relates to nitrogen-containing organosiliconcompounds of general Formula (II) below and to a method formanufacturing such compounds:

where R⁹ is an alicyclic amino group or a heterocyclic amino groupcomposed of 1-4 nitrogen atoms, 3-17 carbon atoms, 0-2 oxygen atoms, and4-34 hydrogen atoms; R³ is a bivalent hydrocarbon group with 1-15 carbonatoms or an alkyleneoxy group of the formula—C_(n)H_(2n)O— where n is1-15; R⁴ is a bivalent hydrocarbon group with 1-15 carbon atoms; R⁵ is aunivalent hydrocarbon group with 1-15 carbon atoms; R⁶ is a univalenthydrocarbon group with 1-15 carbon atoms or an alkoxyalkyl group; R⁷ isa an alkyl group such as methyl or a hydrogen atom; R⁸ is a hydrogenatom, an alkyl group with 1-20 carbon atoms, or an aryl group; m is 0 or1; x is 0-2; and y is 1-5.

The invention also relates to silane coupling agents prepared fromnitrogen-containing organosilicon compounds represented by generalFormulae (I) or (II) above.

In general, the nitrogen-containing organosilicon compounds of thepresent invention are silane compounds represented by general Formulae(I) and (II). In those Formulae, R¹ and R² may designate the same ordifferent univalent hydrocarbon groups with 1-15 carbon atoms includingalkyl groups such as methyl groups, ethyl groups, propyl groups, andbutyl groups; alkenyl groups such as vinyl groups, allyl groups, andbutenyl groups; aryl groups such as phenyl groups, tolyl groups, andxylyl groups; and aralkyl groups such as benzyl groups and phenethylgroups.

Of these groups, most preferred because of availability are alkylgroups, especially methyl or ethyl groups. In the above formulae: R³ isa bivalent hydrocarbon group with 1-15 carbon atoms or an alkyleneoxygroup of the formula —C_(n)H_(2n)O— where n is 1-15, as well as abivalent hydrocarbon group including alkylene groups such as methylenegroups, ethylene groups, propylene groups, pentylene groups, andhexylene groups; arylene groups such as phenylene groups, naphthalenylgroups, and biphenylene groups; phenyl substituted alkylene groups suchas 4,4′-bismethylene phenyl groups, 3,4′-bismethylenephenyl groups, and4,4′-bis-ethylenephenyl groups; alkylene arylene groups such as4,4′-bis-methylenebiphenylene groups; and alkyleneoxy groups such as—CH₂O—, —C₂H₄O—, and —C₃H₆O—. Of these groups, most preferred for easeof synthesis are alkylene groups and alkyleneoxy groups.

In the above formulae, R⁴ indicates bivalent hydrocarbon groups with1-15 carbon atoms including alkylene groups such as methylene groups,ethylene groups, propylene groups, pentylene groups, and hexylenegroups; arylene groups such as phenylene groups, naphthalenyl groups,and biphenylene groups; phenyl substituted groups such as4,4′-bismethylene phenyl groups, 3,4′-bismethylene phenyl groups, and4,4′-bisethylene phenyl groups; and alkylene arylene groups such as4,4′-bismethylene biphenylene groups. Of these, most preferred as beingreadily available are alkylene groups, in particular propylene groups.

In the above formulae, R⁵ designates univalent hydrocarbon groups with1-15 carbon atoms including alkyl groups such as methyl groups, ethylgroups, propyl groups, and butyl groups; alkenyl groups such as vinylgroups, allyl groups, and butenyl groups; aryl groups such as phenylgroups, tolyl groups, and xylyl groups; and aralkyl groups such asbenzyl groups and phenethyl groups.

R⁶ designates univalent hydrocarbon groups with 1-15 carbon atoms oralkoxyalkyl groups including alkyl groups such as methyl groups, ethylgroups, propyl groups, and butyl groups; alkenyl groups such as vinylgroups, allyl groups, and butenyl groups; aryl groups such as phenylgroups, tolyl groups, and xylyl groups; aralkyl groups such as benzylgroups, and phenethyl groups; and alkoxyalkyl groups such asmethoxyethyl groups, and methoxypropyl groups.

When the nitrogen-containing organosilicon compounds of the presentinvention are used as silane coupling agents, better reactivity of thecompounds can be achieved when R⁵ and R⁶ are methyl and ethyl groups.

In the above formulae, R⁷ designates alkyl groups such as methyl groupsor hydrogen atoms; R⁸ designates a hydrogen atom, an alkyl groups with1-20 carbon atoms such as methyl groups, ethyl groups, propyl groups,and butyl groups, or aryl groups with 6-20 carbon atoms such as phenylgroups, tolyl groups, and xylyl groups. In each molecule, the R⁸ groupscan be the same or different. Of these, most preferred because ofavailability are hydrogen atoms. R⁹ is an alicyclic amino group or aheterocyclic amino group with 1-4 nitrogen atoms, 3-17 carbon atoms, 0-2oxygen atoms, and 4-34 hydrogen atoms.

Cyclic structures of these groups contain one or more tertiary aminogroups. Such groups are exemplified by N-cyclopentylamino groups,N-cyclohexylamino groups, N-cycloheptylamino groups,N-(4-methylcyclohexyl)amino groups, and morpholino groups. Of these,most preferred for availability are N-cyclohexylamino groups ormorpholino groups.

In the above formulae, m is 0 or 1; and x is 0-2. Most preferred becauseof availability and reactivity of coupling agents are groups wherein mand x are equal to 0. In the formulae, y is 1-5, preferably 1 or 2. Thefollowing are examples of groups where y is 2:N-ethylene-3-aminopropylene groups,N-ethylene-N′-ethylene-3-aminopropylene groups,N-ethylene-4-aminophenylene groups, andN-ethylene-2-aminoethyl-1-ethylenephenylene groups. Of these,N-ethylene-3-aminopropylene groups are preferred.

The nitrogen-containing organosilicon compounds of the present inventioninclude alkoxysilane compounds such as represented by the followingformulae wherein Me represents the methyl group and Et represents theethyl group:(CH₃)₂NCOC₂H₄NHC₃H₆Si(OC₂H₅)₃(CH₃)₂NCOC₂H₄NHC₂H₄NHC₃H₆Si(OCH₃)₃(C₂H₅)₂NCOC₂H₄NHC₃H₆Si(OC₂H₅)₃(C₂H₅)₂NCOC₂H₄NHC₂H₄NHC₃H₆Si(OC₂H₅)₃(n-C₄H₉)₂NCOC₂H₄NHC₃H₆Si(OC₂H₅)₃(n-C₄H₉)₂NCOC₂H₄NHC₂H₄NHC₃H₆Si(OCH₃)₃(CH₃)₂NC₂H₄COC₂H₄NHC₃H₆Si(OC₂H₅)₃(CH₃)₂NC₂H₄COC₂H₄NHC₂H₄NHC₃H₆Si(OCH₃)₃(CH₃)₂NC₂H₄OCOC₂H₄NHC₃H₆Si(OCH₃)₃(C₂H₅)₂NC₂H₄OCOC₂H₄NHC₃H₆Si(OC₂H₅)₃(n-C₄H₉)₂NC₂H₄OCOC₂H₄NHC₃H₆Si(OC₂H₅)₃(CH₃)₂NC₂H₄OCOC₂H₄NHC₂H₄NHC₃H₆Si(OCH₃)₃

The nitrogen-containing organosilicon compounds of the present inventioncan be obtained by causing an addition reaction between compound (A) ofthe following general formula (IV):

wherein R⁴, R⁵, R⁶, R⁸, x, and y, are the same as defined above;and a compound (B) of the following general formula (III):

wherein R¹, R², R³, R⁷, and m, are the same as defined above;or a compound (B) of the following general formula (V):

wherein R⁹, R³, R⁷, and m, are the same as defined above.

Component (A) represented by the general formula (IV) is a commerciallyavailable organosilicon compound such as 3-aminopropyltrimethoxysilane,3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane,3-aminopropyltri(methoxyethoxy)silane, 4-aminobutyltrimethoxysilane,5-aminopentyltrimethoxysilane,N-(2-aminoethyl)-3-aminopropyltrimethoxysilane,N-(2-aminoethyl)-3-aminopropyltriethoxysilane,N-(2-aminoethyl)-3-aminopropyltri(methoxyethoxy)silane, andN-(2-aminoethyl)-4-aminobutyltrimethoxysilane. Of these, the mostpreferred are 3-aminopropyltrimethoxysilane and3-aminopropyltriethoxysilane.

Component (B) of Formulae (III) or (V) can be a acrylamide or acrylesterwith tertiary amino groups. These compounds are commercially availableand are exemplified by N,N-dimethylacrylamide,N,N-dimethylmethacrylamide, N,N-diethylacrylamide,N,N-dipropylacrylamide, N,N-methylethylacrylamide,N,N-dimethylmethacrylamide, N,N-dibutylmethacrylamide,N-piperazinoacrylamide, N-acryloylmorpholine,N,N-dimethylaminoethylacrylamide, N,N-diethylaminopropylmethacrylamide,2-(dimethylamino)ethyl acrylate, 2-(diethylamino)ethyl acrylate, and2-(dibutylamino)ethyl acrylate. Of these, most preferred areN,N-dimethylacrylamide and N-acryloylmorpholine.

Although a reaction of addition between components A and B can becarried out at room temperature, it is preferred to conduct the reactionwith heating at a temperature not exceeding 150° C., most preferably ata temperature between 60-100° C. It is also preferred to fill theinterior of the reactor with an inert gas such as argon or nitrogen. Theaddition reaction can be carried out as a consecutive reaction or aone-stage reaction. It is preferred to heat one of the components (A) or(B), while the other component is added gradually.

One distinguishing feature of the invention is that when thenitrogen-containing organosilicon compound is used in conjunction withan organic resin to which an amine functions as a curing catalyst, theunfavorable effect of the compound on curability of the resin is reducedbecause of the tertiary amine group on the molecular terminal. Anotherdistinguishing feature of the invention is that the nitrogen-containingorganosilicon compounds can be produced with high yield usingcommercially available starting materials. A further distinguishingfeature of the manufacturing method of the invention is that thereaction can proceed efficiently even without the use of any catalystand any solvent. The manufacturing process can be carried out withoutthe use of any special reactor and can be performed on conventionalequipment.

The nitrogen-containing organosilicon compounds of the invention provideimproved adhesion between various substrates, in particular betweenorganic resins and inorganic materials, or metal materials, when x inthe general Formulae (I) and (II) is 0 or 1. Because of these features,nitrogen-containing organosilicon compounds of the present invention aresuitable for use as surface-treatment agents, adhesion improvers,primers, and silane coupling agents, for improving the properties oforganic resins. The organic resins suitable for purposes of theinvention include epoxy resins, phenol resins, urethane resins, melamineresins, polycarbonate resins, polyethylene resins, polyvinylchlorideresins, and polyamide resins.

In use as silane coupling agents, the nitrogen-containing organosiliconcompounds of general Formulae (I) or (II) may be diluted with water oran organic solvent. The organic solvent suitable for this purposeinclude methanol, ethanol, or similar water soluble organic solvent. Thecoupling agent can be applied onto the surface of substrate to betreated or it can be added to the organic resins. The former method ispreferred.

Several processes can be used for applying the coupling agent. Thecoupling agent alone can be sprayed onto the substrate; the couplingagent can be diluted in an organic solvent and the solution can besprayed onto the surface of the substrate; the coupling agent can bediluted in a water/organic solvent mixture and sprayed onto thesubstrate; the substrate can be impregnated with the treatment solutionobtained with the coupling agent and an organic solvent; and thesubstrate can be impregnated with the treatment liquid obtained bymixing the coupling agent with the water/organic solvent mixture.

These treatments can be completed by the application of heat.

Substrates which can be treated with the silane coupling agent of theinvention include powdered materials such as fumed silica, wet-processsilica, baked silica, fumed titanium dioxide, powdered quartz,diatomaceous earth, aluminum hydroxide, aluminum oxide, magnesium oxide,aluminosilicate, iron oxide, zinc oxide, calcium oxide, zinc carbonate,mica, and magnesium carbonate; fibrous materials such as glass fiber,Nylon fiber, and carbon fiber; and plates such as glass plates, copperplates, iron plates, stainless-steel plates, and aluminum plates.

EXAMPLES

The following examples are set forth in order to illustrate theinvention in more detail.

Practical Example 1

A four neck flask equipped with a thermometer, stirrer, and cooler, wasfilled with 156.7 parts by weight of 3-aminopropyltriethoxysilane, andthe content of the flask was heated in a nitrogenous atmosphere to 70°C. Then, 77.2 parts by weight of N,N-dimethylacrylamide was addeddropwise over 30 minutes, and the mixture was stirred and heated for 8hours at 100° C. The reaction mixture was distilled under a reducedpressure at 138° C. and 1.3 hPa to produce 170.2 parts by weight of acolorless transparent liquid, at a yield of 75 percent. Results of ¹³Cnuclear magnetic resonance spectral analysis (NMR), infrared analysis(IR), and GC/MS analysis, defined the product as a nitrogen-containingorganosilicon compound of the formula(CH₃)₂NCOC₂H₄NHC₃H₆Si(OC₂H₅)₃.

Practical Example 2

A four neck flask equipped with a thermometer, stirrer, and cooler, wasfilled with 298.1 parts by weight of 3-aminopropyltrimethoxysilane, andthe content of the flask was heated in a nitrogenous atmosphere to 70°C. Then, 181.0 parts by weight of N,N-dimethylacrylamide was addeddropwise over 60 minutes, and the mixture was stirred and heated for 8hours at 100° C. The reaction mixture was distilled under a reducedpressure at 130° C. and 1.3 hPa to produce 360.5 parts by weight of acolorless transparent liquid, at a yield of 78 percent. Results of ¹³Cnuclear magnetic resonance spectral analysis (NMR), infrared analysis(IR), and GC/MS analysis, defined the product as a nitrogen-containingorganosilicon compound of the formula(CH₃)₂NCOC₂H₄NHC₃H₆Si(OCH₃)₃.

Practical Example 3

A four neck flask equipped with a thermometer, stirrer, and cooler, wasfilled with 33.21 parts by weight of 3-aminopropyltriethoxysilane, andthe content of the flask was heated in a nitrogenous atmosphere to 70°C. Then, 23.3 parts by weight of N-acryloyl morpholine was addeddropwise over 10 minutes, and the mixture was stirred and heated for 3hours at 100° C. The reaction mixture was distilled under a reducedpressure at 130° C. and 1.3 hPa to produce 53.7 parts by weight of ayellow transparent liquid, at a yield of 95 percent. Results of ¹³Cnuclear magnetic resonance spectral analysis (NMR), and infraredanalysis (IR), defined the product as a nitrogen-containingorganosilicon compound of the formula

where Et represents the ethyl group.

Practical Example 4

A four neck flask equipped with a thermometer, stirrer, and cooler, wasfilled with 33.21 parts by weight of 3-aminopropyltriethoxysilane, andthe content of the flask was heated in a nitrogenous atmosphere to 70°C. Then, 23.6 parts by weight of 2-(dimethylamino) ethylacrylate wasadded dropwise over 10 minutes, and the mixture was stirred and heatedfor 3 hours at 100° C. The reaction mixture was distilled under areduced pressure at 130° C. and 1.3 hPa to produce 53.7 parts by weightof a yellow transparent liquid, at a yield of 96 percent. Results of ¹³Cnuclear magnetic resonance spectral analysis (NMR), and infraredanalysis (IR), defined the product as a nitrogen-containingorganosilicon compound of the formula(CH₃)₂NC₂H₄OCOC₂H₄NHC₃H₆Si(OC₂H₅)₃.

Practical Example 5

A four neck flask equipped with a thermometer, stirrer, and cooler, wasfilled with 222.4 parts by weight ofN-(2-aminoethyl)-3-aminopropyltrimethoxysilane, and the content of theflask was heated in a nitrogenous atmosphere to 70° C. Then, 109.0 partsby weight of N,N-dimethylacrylamide was added dropwise over 30 minutes,and the mixture was stirred and heated for 8 hours at 100° C. Thereaction mixture was distilled under a reduced pressure at 130° C. and1.3 hPa to produce 324.8 parts by weight of a yellowish transparentliquid, at a yield of 98 percent. Results of ¹³C nuclear magneticresonance spectral analysis (NMR), and infrared analysis (IR), definedthe product as a nitrogen-containing organosilicon compound of theformula(CH₃)₂NCOC₂H₄NHC₂H₄NHC₃H₆Si(OCH₃)₃.

Practical Example 6

The nitrogen-containing organosilicon compounds obtained in PracticalExamples 1-5 were diluted with a mixture of water and ethanol in a 1:1weight ratio of water to ethanol. This produced treatment liquids with aconcentration of 0.4 weight percent of the organosilicon compound. Glassplates were immersed for 10 seconds in these solutions, respectively,and then dried for one hour at 120° C. Then, a curable epoxy resincomposition consisting of 100 parts by weight of a bisphenol type Aepoxy resin sold under the name EPICOAT 828 having an epoxy equivalentof 185; 8 parts by weight of dicyandiamide; and 0.4 parts by weight ofN-dimethylbenzylamine, was applied to the surfaces of the glass plates.The coatings were dried for 90 minutes at 170° C. There was obtainedcured epoxy resin coatings firmly adhered to the glass surface, having acylindrical shape with a 5 mm diameter and 5 mm height.

The coated samples were analyzed for adhesion of the cured epoxy resinusing a durometer. The adhesive force was also measured prior and aftera Pressure Cooker Test (PCT) which consisted of heating the samples for24 hours at 121° C. and 100% Relative Humidity. The results of the PCTtests are shown in Table 1.

In Comparative Examples, adhesive force was measured using silanecoupling agents as noted below:

Comparative Example 1

H₂N CONHC₃H₆Si(OC₂H₅)₃

Comparative Example 2

PhNHC₃H₆Si(OCH₃)₃ where Ph is phenyl.

Comparative Example 3

C₁₈H₃₇NHCOC₂H₄NHC₃H₆Si(OC₂H₅)₃.

The results are shown in Table 1.

TABLE 1 Adhesive Force (kgf/cm²) Example Prior to PCT After PCTPractical Example 1 140 167 Practical Example 2 157 160 PracticalExample 3 132 128 Practical Example 4 140 139 Practical Example 5 155163 Comparative Example 1 (*) 118 73 Comparative Example 2 (**) 130 79Comparative Example 3 (***) 115 85 In Table 1, (*) is the compoundH₂NCONHC₃H₆Si(OC₂H₅)₃; (**) is the compound PhNHC₃H₆Si(OCH₃)₃; and (***)is the compound C₁₈H₃₇NHCOC₂H₄NHC₃H₆Si(OC₂H₅)₃.

INDUSTRIAL APPLICABILITY

In view of the above, it should be apparent that the nitrogen-containingorganosilicon compounds of the present invention are new and novelcompounds containing tertiary-amine and carbonyl groups; that the methodfor preparing the nitrogen-containing compound provides a high yield;and that when the compounds are used as silane coupling agents, there isobtained improved adhesion between various substrates.

Other variations may be made in compounds, compositions, and methodsdescribed herein without departing from the essential features of theinvention. The embodiments of the invention specifically illustratedherein are exemplary only and not intended as limitations on their scopeexcept as defined in the appended claims.

1. A nitrogen-containing organosilicon compound of the formula:

wherein R⁹ is an alicyclic amino group or a heterocyclic amino groupcontaining 1 nitrogen atom, 4-5 carbon atoms, 0-1 oxygen atoms, and 8 or10 hydrogen atoms; R³ is a bivalent hydrocarbon group with 1-15 carbonatoms, or an alkyleneoxy group of the formula —C_(n)H_(2n)O—where n is1-15; R⁴ is a bivalent hydrocarbon group with 1-15 carbon atoms; R⁵ is aunivalent hydrocarbon group with 1-15 carbon atoms; R⁶ is a univalenthydrocarbon group with 1-15 carbon atoms or an alkoxyalkyl group; R⁷ isan alkyl group or a hydrogen atom; R⁸ is a hydrogen atom, an alkyl groupwith 1-20 carbon atoms, or an aryl group; m is 0 or 1; x is 0-2; and yis 1-5.
 2. A method of manufacturing a nitrogen-containing organosiliconcompound of claim 1 comprising the addition reaction of a compound ofthe formula:

and a compound of the formula:

wherein R⁹ is an alicyclic amino group or a heterocyclic amino groupcontaining 1 nitrogen atom, 4-5 carbon atoms, 0-1 oxygen atoms, and 8 or10 hydrogen atoms; R³ is a bivalent hydrocarbon group with 1-15 carbonatoms, or an alkyleneoxy group of the formula —C_(n)H_(2n)O—where n is1-15; R⁴ is a bivalent hydrocarbon group with 1-15 carbon atoms; R⁵ is aunivalent hydrocarbon group with 1-15 carbon atoms; R⁶ is a univalenthydrocarbon group with 1-15 carbon atoms or an alkoxyalkyl group; R⁷ isan alkyl group or a hydrogen atom; R⁸ is a hydrogen atom, an alkyl groupwith 1-20 carbon atoms, or an aryl group; m is 0 or 1; x is 0-2; and yis 1-5.
 3. A method of treating a surface comprising applying to thesurface a nitrogen-containing organosilicon compound according toclaim
 1. 4. A method of treating a surface comprising applying to thesurface a solution containing the nitrogen-containing organosiliconcompound according to claim 1.